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Title: What is the nucleophilic atom in the Williamson ether synthesis? Post by: lethalheritage on Sep 23, 2012 What element is the nucleophilic atom in the Williamson ether synthesis?
Title: What is the nucleophilic atom in the Williamson ether synthesis? Post by: lethallunatic117 on Sep 23, 2012 The Williamson ether synthesis is a standard SN2 mechanism reaction. That being said, just think about it. A primary alcohol becomes an alkoxide ion and reacts with an alkyl halide to form an ether. Since alkyl halides, and most halides (Cl- and Br-) make great leaving groups, the alkoxide acts as the nucleophile.
An example using ethanol and methyl bromide (alkyl chlorides are kinda pesky, and often need a catalyst): 2 H3C-CH2-OH + 2Na --> 2 H3C-CH2-O-Na+ + H2(g). (formation of the alkoxide ion) H3C-CH2-O-Na+ + CH3-Br <---> H3C-CH2-O---CH3---Br (the transition product, according to SN2) <---> H3C-CH2-O-CH3 + Br- Hope this makes sense. |